Composition and organic light-emitting device including the same

Abstract

A composition including a platinum-containing organometallic compound, a first compound, a second compound, and a third compound, and an organic light-emitting device including the same wherein the composition does not comprise iridium,

• • the Pt-containing organometallic compound, the first compound, the second compound, and the third compound are different from each other,
  • the first compound comprises at least one electron transport moiety,
  • the second compound and the third compound do not include a metal,
  • each of an absolute value of a homo energy level of the second compound and an absolute value of a homo energy level of the third compound is 5.30 eV to 5.85 eV,
  • the difference between the absolute value of the homo energy level of the second compound and the absolute value of the homo energy level of the third compound is 0.01 eV to 0.30 eV.

Description

CROSS-REFERENCE TO RELATED APPLICATION

This application claims the priority to and the benefit of Korean Patent Application No. 10-2019-0078954, filed on Jul. 1, 2019, in the Korean Intellectual Property Office, and all the benefits accruing under 35 U.S.C. § 119, the content of which is incorporated herein in its entirety by reference.

BACKGROUND

1. Field

One or more embodiments relate to a composition and an organic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices, which have better characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed, and produce full-color images.

In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.

SUMMARY

One or more embodiments relate to a novel composition and an organic light-emitting device including the same.

Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.

An aspect of the present disclosure provides a composition including:

a platinum (Pt)-containing organometallic compound, a first compound, a second compound, and a third compound,

wherein the composition does not include iridium (Ir),

the Pt-containing organometallic compound, the first compound, the second compound, and the third compound are different from each other,

the first compound includes at least one electron transport moiety,

the second compound and the third compound do not include a metal,

each of an absolute value of a highest occupied molecular orbital (HOMO) energy level of the second compound and an absolute value of a HOMO energy level of the third compound is 5.30 eV to 5.85 eV,

the difference between the absolute value of the HOMO energy level of the second compound and the absolute value of the HOMO energy level of the third compound is 0.01 eV to 0.30 eV, and

each of the HOMO energy level of the second compound and the HOMO energy level of the third compound is measured using a photoelectron spectrometer in air.

Another aspect of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the composition.

BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with FIGURE which is a schematic view of an organic light-emitting device according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the FIGURES, to explain aspects of the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present therebetween In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

It will be understood that, although the terms “first,” “second,” “third” etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section Thus, “a first element,” “component,” “region,” “layer” or “section” discussed below could be termed a second element, component, region, layer or section without departing from the teachings herein.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “an,” “the,” and “at least one” do not denote a limitation of quantity, and are intended to cover both the singular and plural, unless the context clearly indicates otherwise. For example, “an element” has the same meaning as “at least one element,” unless the context clearly indicates otherwise.

“Or” means “and/or.” As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

Furthermore, relative terms, such as “lower” or “bottom” and “upper” or “top,” may be used herein to describe one element's relationship to another element as illustrated in the FIGURES. It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the FIGURES. For example, if the device in one of the FIGURES is turned over, elements described as being on the “lower” side of other elements would then be oriented on “upper” sides of the other elements. The exemplary term “lower,” can therefore, encompasses both an orientation of “lower” and “upper,” depending on the particular orientation of the FIGURE. Similarly, if the device in one of the FIGURES is turned over, elements described as “below” or “beneath” other elements would then be oriented “above” the other elements. The exemplary terms “below” or “beneath” can, therefore, encompass both an orientation of above and below.

“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10% or 5% of the stated value.

Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.

A composition according to an aspect of the present disclosure may include a platinum (Pt)-containing organometallic compound, a first compound, a second compound, and a third compound. The Pt-containing organometallic compound, the first compound, the second compound, and the third compound will be described in detail below.

The composition may not include iridium (Ir).

The Pt-containing organometallic compound, the first compound, the second compound, and the third compound included in the composition may be different from each other. That is, the composition may include 4 or more different compounds.

In one or more embodiments, the Pt-containing organometallic compound may include Pt and an organic ligand, and the Pt and the organic ligand may form 1, 2, 3, or 4 cyclometallated ring(s).

In one or more embodiments, the Pt-containing organometallic compound may include Pt and a tetradentate organic ligand, and the Pt and the tetradentate organic ligand may form 3 or 4 cyclometallated rings.

In one or more embodiments, the Pt-containing organometallic compound may include Pt and a tetradentate organic ligand, and the tetradentate organic ligand may include a benzimidazole group and a pyridine group. Each of the benzimidazole group and the pyridine group may be directly linked to the Pt of the Pt-containing organometallic compound.

An absolute value of a highest occupied molecular orbital (HOMO) energy level of the Pt-containing organometallic compound may be 5.25 eV to 5.55 eV.

The first compound may include at least one electron transport moiety.

In the present specification, the term “electron transport moiety” may be a cyano group, a fluoro group, a π-electron-deficient nitrogen-containing cyclic group, a group represented by one of the following formulae, or any combination thereof:

##STR00001##

In the formulae above, *, *′, and *″ each indicate a binding site to a neighboring atom.

Neither of the second compound and third compound may include a metal.

For example, each of the absolute value of the HOMO energy level of the second compound and the absolute value of the HOMO energy level of the third compound may be 5.30 eV to 5.85 eV, for example, 5.50 eV to 5.75 eV.

The difference between the absolute value of the HOMO energy level of the second compound and the absolute value of the HOMO energy level of the third compound may be 0.01 eV to 0.30 eV, for example, 0.05 eV to 0.10 eV. When the difference between the absolute value of the HOMO energy level of the second compound and the absolute value of the HOMO energy level of the third compound is satisfied within the ranges above, the effective HOMO energy disorder parts of the Gaussian disorder model (GDM) are increased to facilitate hole transfer among the Pt-containing organometallic compound, the second compound, and the third compound, and the positive polaron density of the Pt-containing organometallic compound may be maintained at a high level. Accordingly, an electronic device, for example, an organic light-emitting device, including the composition may have high external quantum luminescence efficiency, low driving voltage, and high lifetime characteristics.

In one or more embodiments, at least one of the second compound and the third compound (for example, all of the second compound and the third compound) may not include the electron transport moiety.

In one or more embodiments, the first compound may include at least one π-electron-rich C₃-C₃₀ cyclic group and at least one electron transport moiety, and at least one of the second compound and the third compound (for example, all of the second compound and the third compound) may each independently include at least one π-electron-rich C₃-C₃₀ cyclic group and may not include the electron transport moiety.

In one or more embodiments, at least one of the second compound and the third compound (for example, all of the second compound and the third compound) may each independently be:

i) a condensed ring in which one or more fifth rings and one or more sixth rings are condensed with each other,

ii) a group represented by

##STR00002##
or

iii) any combination thereof,

wherein the fifth ring may be a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, or a silole group,

the sixth ring may be a π-electron-rich C₃-C₃₀ cyclic group, and

*, *′, and *″ each indicate a binding site to a neighboring atom.

In the present specification, the HOMO energy level of each of the Pt-containing organometallic compound, the first compound, the second compound, and the third compound may be measured using a photoelectron spectrometer (for example, AC3 manufactured by RIKEN KEIKI Co., Ltd.) in air.

In one or more embodiments, the Pt-containing organometallic compound may be an organometallic compound represented by Formula 1, and/or

the first compound may be a compound represented by Formula 2, and/or

the second compound and the third compound may each independently be a compound represented by one of Formulae 3-1 to 3-4:

##STR00003##

In Formula 1, M may be Pt.

In Formula 1, Y₁ to Y₄ may each independently be a chemical bond (e.g., a covalent bond or a coordinate bond), O, S, N(R_a), C(R_a)(R_b), or Si(R_a)(R_b). When Y₁ is a chemical bond, X₁ may directly bind to M, when Y₂ is a chemical bond, X₂ may directly bind to M, when Y₃ is a chemical bond, X₃ may directly bind to M, and when Y₄ is a chemical bond, X₄ may directly bind to M.

For example, in Formula 1, Y₁ may be O or S, and Y₂ to Y₄ may be chemical bonds.

In Formula 1, X₁ to X₄ may each independently be C or N.

In one or more embodiments, in Formula 1, Y₁ may be O or S, Y₂ to Y₄ may each be a chemical bond, X₁ and X₃ may each be C, and X₂ and X₄ may each independently be N, but embodiments of the present disclosure are not limited thereto.

In Formula 1, two bonds among a bond between M and Y₁ or X₁, a bond between M and Y₂ or X₂, a bond between M and Y₃ or X₃, and a bond between M and Y₄ or X₄ may be coordinate bonds, and the other two bonds may each be covalent bonds. Therefore, the organometallic compound represented by Formula 1 may be electrically neutral.

For example, Y₁ may not be a chemical bond. Y₂ to Y₄ may each be a chemical bond. A bond between Y₁ and M and a bond between X₃ and M may be covalent bonds. A bond between X₂ and M and a bond between X₄ and M may be coordinate bonds.

In Formula 1, ring CY₁ to ring CY₄ may each independently be a C₅-C₃₀ carbocyclic group or a C₁-C₃₀ heterocyclic group.

In one or more embodiments, in Formula 1, ring CY₁ to ring CY₄ may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which one or more first rings are condensed with one or more second rings, wherein

the first ring may be a cyclohexane group, a cyclohexene group, an adamantane group, a norbornane group, a norbornene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, and

the second ring may be a cyclopentane group, a cyclopentene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an azasilole group, an oxadiazole group, or thiadiazole group.

In one or more embodiments, in Formula 1, ring CY₁ to ring CY₄ may each independently be a cyclopentene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.

In one or more embodiments,

ring CY₁ in Formula 1 may be a group represented by one of Formulae CY1-1 to CY1-26, and/or

ring CY₂ in Formula 1 may be a group represented by one of Formulae CY2-1 to CY2-19, and/or

ring CY₃ in Formula 1 may be a group represented by one of Formulae CY3-1 to CY3-18, and/or

ring CY₄ in Formula 1 may be a group represented by one of Formulae CY4-1 to CY4-26:

##STR00004## ##STR00005## ##STR00006## ##STR00007## ##STR00008## ##STR00009## ##STR00010## ##STR00011## ##STR00012## ##STR00013## ##STR00014##

In Formulae CY1-1 to CY1-26, X₁₉ may be O, S, C(R₁₇)(R₁₈), Si(R₁₇)(R₁₈), or N-[(L₁₉)_b19-(R₁₉)_c19], R₁₇ to R₁₉ may each be the same as defined in connection with R₁, L₁₉, b19, and c19 may each be the same as defined in connection with L₁, b1, and c1, respectively, * indicates a binding site to M or Y₁ in Formula 1, and *′ indicates a binding site to T₁ or ring CY₂ in Formula 1.

In Formulae CY2-1 to CY2-19, X₂₉ may be O, S, C(R₂₇)(R₂₈), Si(R₂₇)(R₂₈), or N-[(L₂₉)_b29-(R₂₉)_c29], R₂₇ to R₂₉ may each be the same as defined in connection with R₂, L₂₉, b29, and c29 may each be the same as defined in connection with L₂, b2, and c2, respectively, * indicates a binding site to M or Y₂ in Formula 1, *′ indicates a binding site to T₁ or ring CY₁ in Formula 1, and *″ indicates a binding site to T₂ or ring CY₃ in Formula 1.

In Formulae CY3-1 to CY3-18, X₃₉ may be O, S, C(R₃₇)(R₃₈), Si(R₃₇)(R₃₈), or N-[(L₃₉)_b39-(R₃₉)_c39], R₃₇ to R₃₉ may each be the same as defined in connection with R₃, L₃₉, b39, and c39 may each be the same as defined in connection with L₃, b3, and c3, respectively, * indicates a binding site to M or Y₃ in Formula 1, *″ indicates a binding site to T₂ or ring CY₂ in Formula 1, and *′ indicates a binding site to T₃ or ring CY₄ in Formula 1.

In Formulae CY4-1 to CY4-26, X₄₉ may be O, S, C(R₄₇)(R₄₈), Si(R₄₇)(R₄₈), or N-[(L₄₉)_b49-(R₄₉)_c49], R₄₇ to R₄₉ may each be the same as defined in connection with R₄, L₄₉, b49, and c49 may each be the same as defined in connection with L₄, b4, and c4, respectively, * indicates a binding site to M or Y₄ in Formula 1, and *′ indicates a binding site to T₃ or ring CY₃ in Formula 1.

In Formula 1, T₁ may be a single bond, a double bond, *—N(R₅₁)—*′, *—B(R₅₁)—*′, *—P(R₅₁)—*′, *—C(R₅₁)(R₅₂)—*′, *—Si(R₅₁)(R₅₂)—*′, *—Ge(R₅₁)(R₅₂)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*, *—C(R₅₁)=*′, *═C(R₅₁)—*′, *—C(R₅₁)═C(R₅₂)—*′, *—C(═S)—*′, or *—C≡C—*′, T₂ may be a single bond, a double bond, *—N(R₅₃)—*′, *—B(R₅₃)—*′, *—P(R₅₃)—*′, *—C(R₅₃)(R₅₄)—*′, *—Si(R₅₃)(R₅₄)—*′, *—Ge(R₅₃)(R₅₄)—*′, *—S—*′, *—Se—*′, *—O—*, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₅₃)=*′, *═C(R₅₃)—*′, *—C(R₅₃)═C(R₅₄)—*′, *—C(═S)—*′, or *—C≡C—*′, and T₃ may be a single bond, a double bond, *—N(R₅₅)—*′, *—B(R₅₅)—*′, *—P(R₅₅)—*′, *—C(R₅₅)(R₅₆)—*′, *—Si(R₅₅)(R₅₆)—*, *—Ge(R₅₅)(R₅₆)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₅₅)=*′, *═C(R₅₅)—*′, *—C(R₅₅)═C(R₅₆)—*′, *—C(═S)—*′, or *—C≡C—*′.

For example, in Formula 1, ring CY₂ may be a benzoxazole group, a benzothiazole group, or a benzimidazole group, and T₁ to T₃ may each be a single bond.

In one or more embodiments, in Formula 1, ring CY₂ may be a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, or an azadibenzothiophene group, and at least one of T₁ to T₃ may not be a single bond.

In Formula 2, Het1 may be a π-electron-deficient nitrogen-containing C₁-C₃₀ cyclic group.

In Formula 3-1, ring CY₇₁ and ring CY₇₂ may each independently be a π-electron-rich C₃-C₃₀ cyclic group, and ring CY₇₁ and ring CY₇₂ may optionally be linked to each other via a π-electron-rich C₃-C₃₀ cyclic group unsubstituted or substituted with at least one R_10a.

In the present specification, the term “π-electron-deficient nitrogen-containing cyclic group” refers to a heterocyclic group including *═N—*′ as a ring-forming moiety, and may be, for example, i) a third ring, ii) a condensed ring in which two or more third rings are condensed with each other, or iii) a condensed ring in which one or more third rings are condensed with one or more fourth rings. In the present specification, the term “π-electron-deficient nitrogen-containing C₁-C₃₀ cyclic group” refers to a π-electron-deficient nitrogen-containing cyclic group having 1 to 30 carbon atoms.

In the present specification, the term “π-electron-rich cyclic group” refers to a carbocyclic or heterocyclic group not including *═N—*′ as a ring-forming moiety, and may be, for example, i) a fourth ring or ii) a condensed ring in which two or more fourth rings are condensed with each other. In the present specification, the term “π-electron-rich C₃-C₃₀ cyclic group” refers to a π-electron-rich cyclic group having 3 to 30 carbon atoms.

In the present specification, the “third ring” may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, an azasilole group, a triazole group, a tetrazole group, an oxadiazole group, a thiadiazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, or a triazine group.

In the present specification, the “fourth ring” may be a benzene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, or a silole group.

The “π-electron-deficient nitrogen-containing cyclic group” may be, for example, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridopyrazine group, a pyrrolophenanthrene group, a furanophenanthrene group, or a thienophenanthrene group, but embodiments of the present disclosure are not limited thereto.

The “π-electron-rich cyclic group” may be, for example, a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphtho pyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, an acridine group, a dihydroacridine group, a benzonaphthofuran group, a benzonaphthothiophene group, an (indolo)phenanthrene group, a (benzofurano)phenanthrene group, or a (benzothieno)phenanthrene group, but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, Het1 in Formula 2 may be a group represented by one of Formulae 2-1 to 2-42:

##STR00015## ##STR00016## ##STR00017## ##STR00018##

In one or more embodiments, a group represented by

##STR00019##
Formula 3-1 may be a group represented by one of Formulae 3(1) to 3(96):

##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034##

In Formulae 3(1) to 3(96),

X₇₁ may be the same as described below,

X₇₂ may be O, S, N(R_78a), C(R_78a)(R_78b), or Si(R_78a)(R_78b),

X₇₃ may be O, S, N(R_79a), C(R_79a)(R_79b), or Si(R_79a)(R_79b), and

R_78a, R_78b, R_79a, and R_79b may each be the same as defined in connection with R₇₁.

In Formula 3-1, X₇₁ may be O, S, N-(L₇₅)_b75-(R₇₅)_a75, C(R₇₅)(R₇₆), or Si(R₇₅)(R₇₆).

In Formula 3-1, L₇₉ may be a single bond or a π-electron-rich C₃-C₃₀ cyclic group unsubstituted or substituted with at least one R_10a; or may be absent.

In Formula 2, n may be an integer from 1 to 10. When n is 2 or more, two or more groups represented by *-(L₆₁)_b61-(R₆₁)_a61 may be identical to or different from each other. For example, n in Formula 3 may be 1, 2, or 3, but embodiments of the present disclosure are not limited thereto.

In Formula 3-1, m may be 1, 2, or 3. When m is 1, L₇₉ may be absent. For example, m in Formula 3-1 may be 1 or 2.

In Formulae 1, 2, and 3-1 to 3-4, L₁ to L₄, L₆₁, L₇₅, and L₈₁ to L₈₇ may each independently be a single bond, a C₅-C₃₀ carbocyclic group unsubstituted or substituted with at least one R_10a, or a C₁-C₃₀ heterocyclic group unsubstituted or substituted with at least one R_10a.

For example, in Formulae 1, 2, and 3-1 to 3-4, L₁ to L₄, L₆₁, L₇₅, and L₈₁ to L₈₇ may each independently be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphtho pyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, an acridine group, a dihydroacridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a benzonaphthofuran group, a benzonaphthothiophene group, an (indolo)phenanthrene group, a (benzofurano)phenanthrene group, or a (benzothieno)phenanthrene group, each unsubstituted or substituted with at least one R_10a.

In one or more embodiments, L₇₅ and L₈₁ to L₈₇ in Formulae 3-1 to 3-4 may each independently be a π-electron-rich C₃-C₃₀ cyclic group unsubstituted or substituted with at least one R_10a.

In one or more embodiments, L₇₅ and L₈₁ to L₈₇ in Formulae 3-1 to 3-4 may each independently be a benzene group unsubstituted or substituted with at least one R_10a, or a group represented by one of Formulae 3(1) to 3(96) unsubstituted or substituted with least one R_10a, but embodiments of the present disclosure are not limited thereto.

In Formulae 1, 2, and 3-1 to 3-4, b1 to b4, b61, b75, and b81 to b87 each indicate the numbers of L₁ to L₄, L₆₁, L₇₅, and L₈₁ to L₈₇, respectively, and may each independently be one of an integer from 1 to 10 (e.g., 1, 2, or 3).

In Formulae 1, 2, and 3-1 to 3-4, R_a, R_b, R₁ to R₄, R₅₁ to R₅₆, R₆₁, R₆₂, R₇₁, R₇₂, R₇₅, R₇₆, and R₈₁ to R₈₆ may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉). Q₁ to Q₉ may be the same as described below.

In one or more embodiments, R_a, R_b, R₁ to R₄, R₅₁ to R₅₆, R₆₁, R₆₂, R₇₁, R₇₂, R₇₅, R₇₆, and R₈₁ to R₈₆ in Formulae 1, 2, and 3-1 to 3-4 may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF₅, C₁-C₂₀ alkyl group, or a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group or a C₁-C₂₀ alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀ alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1] a hexyl group, a bicyclo[2.2.1] a heptyl group, a bicyclo[2.2.2] an octyl group, a phenyl group, a (C₁-C₂₀ alkyl) a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀ alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, —Si(Q₃₃)(Q₃₄)(Q₃₅), or any combination thereof; or

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —Ge(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉), or —P(Q₈)(Q₉), and

Q₁ to Q₉ and Q₃₃ to Q₃₅ may each independently be:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, or —CD₂CDH₂, or

an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C₁-C₁₀ alkyl group, a phenyl group, or any combination thereof.

In one or more embodiments, R_a, R_b, R₁ to R₄, R₅₁ to R₅₆, R₆₁, R₆₂, R₇₁, R₇₂, R₇₅, R₇₆, and R₆₁ to R₆₆ in Formulae 1, 2, and 3-1 to 3-4 may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —SF₅, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a group represented by one of Formulae 9-1 to 9-66, a group represented by one of Formulae 9-1 to 9-66 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-249, a group represented by one of Formulae 10-1 to 10-249 in which at least one hydrogen is substituted with deuterium, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), or —B(Q₆)(Q₇) (wherein Q₁ to Q₇ may each be the same as described above):

##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079##

In Formulae 9-1 to 9-66 and 10-1 to 10-249, * indicates a binding site to a neighboring atom, Ph indicates a phenyl group, and TMS indicates a trimethylsilyl group.

The “group represented by one of Formulae 9-1 to 9-66 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 9-501 to 9-552:

##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085##

The “group represented by one of Formulae 10-1 to 10-249 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-510:

##STR00086##

In Formula 1, c1 to c4 each indicate the numbers of R₁ to R₄, respectively, and may each independently be an integer from 1 to 10.

In Formulae 1, 2, and 3-1 to 3-4, a1 to a4, a61, a62, a71, a72, a75, and a81 to a86 may each independently be one of an integer from 0 to 20.

In one or more embodiments, R₇₁, R₇₂, R₇₅, R₇₆, and R₈₁ to R₈₆ in Formulae 3-1 to 3-4 may each independently be hydrogen, deuterium, a C₁-C₂₀ alkyl group, a π-electron-rich C₃-C₃₀ cyclic group unsubstituted or substituted with at least one R_10a, —N(Q₁)(Q₂), or —Si(Q₃)(Q₄)(Q₅), but embodiments of the present disclosure are not limited thereto.

In Formula 1, two or more of R_a, R_b, R₁ to R₄, and R₅₁ to R₅₆ may optionally be linked to form a C₅-C₃₀ carbocyclic group unsubstituted or substituted with at least one R_10a or a C₁-C₃₀ heterocyclic group unsubstituted or substituted with at least one R_10a.

In the present specification, R_10a may be the same as defined in connection with R₁.

In the present specification, unless otherwise described, *, *′, and *″ each indicate a binding site to a neighboring atom.

In one or more embodiments, in Formula 1,

a1 to a4 may each independently be one of an integer from 1 to 20, and

at least one of R₁ to R₄ may each independently be a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), or —B(Q₆)(Q₇).

In one or more embodiments, in Formula 1,

1) ring CY₂ may be a benzoxazole group, a benzothiazole group, a benzimidazole group, a benzazasilole group, or a benzopyrrole group, a1 to a4 may each independently be one of an integer from 1 to 20, and at least one of R₁ to R₄ may each independently be a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or

2) ring CY₂ may be a pyridine group, a1 to a4 may each independently be one of an integer from 1 to 20, and at least one of R₁ to R₄ may each independently be a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), or —B(Q₆)(Q₇).

In one or more embodiments,

L₇₅, L₇₉, and L₈₁ to L₈₇ in Formulae 3-1 to 3-4 may each independently be a π-electron-rich C₃-C₃₀ cyclic group unsubstituted or substituted with deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a di(C₁-C₁₀ alkyl)fluorenyl group, a di(C₆-C₆₀ aryl)fluorenyl group, a dibenzosilolyl group, a di(C₁-C₁₀ alkyl)dibenzosilolyl group, a di(C₆-C₆₀ aryl)dibenzosilolyl group, a carbazolyl group, a (C₁-C₁₀ alkyl)carbazolyl group, a (C₆-C₆₀ aryl)carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, —N(Q₃₁)(Q₃₂), or any combination thereof; or L₇₉ in Formula 3-1 may be a single bond, and/or

R₇₁, R₇₂, R₇₅, R₇₆, and R₈₁ to R₈₆ in Formulae 3-1 to 3-4 may each independently be:

hydrogen or deuterium;

a C₁-C₂₀ alkyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a di(C₁-C₁₀ alkyl)fluorenyl group, a di(C₆-C₆₀ aryl)fluorenyl group, a dibenzosilolyl group, a di(C₁-C₁₀ alkyl)dibenzosilolyl group, a di(C₆-C₆₀ aryl)dibenzosilolyl group, a carbazolyl group, a (C₁-C₁₀ alkyl)carbazolyl group, a (C₆-C₆₀ aryl)carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, —N(Q₃₁)(Q₃₂), or any combination thereof;

a π-electron-rich C₃-C₃₀ cyclic group unsubstituted or substituted with deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a di(C₁-C₁₀ alkyl)fluorenyl group, a di(C₆-C₆₀ aryl)fluorenyl group, a dibenzosilolyl group, a di(C₁-C₁₀ alkyl)dibenzosilolyl group, a di(C₆-C₆₀ aryl)dibenzosilolyl group, a carbazolyl group, a (C₁-C₁₀ alkyl)carbazolyl group, a (C₆-C₆₀ aryl)carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, —N(Q₃₁)(Q₃₂), or any combination thereof; or

—N(Q₁)(Q₂),

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, at least one of the second compound and the third compound (for example, all of the second compound and the third compound) may include a carbazole group.

In one or more embodiments, at least one of the second compound and the third compound may each independently be the compound represented by Formula 3-1, wherein X₇₁ in Formula 3-1 may be N-(L₇₅)_b75-(R₇₅)_a75.

In one or more embodiments, at least one of the second compound and the third compound may not include a carbazole group.

In one or more embodiments, at least one of the second compound and the third compound may each independently be the compound represented by one of Formulae 3-2 to 3-4.

In one or more embodiments, at least one of the second compound and the third compound may each independently be the compound represented by one of Formulae 3-2 to 3-4, wherein the compounds represented by Formulae 3-2 to 3-4 may include a carbazole group.

In one or more embodiments, at least one of the second compound and the third compound may each independently be the compound represented by one of Formulae 3-2 to 3-4, and the compounds represented by Formulae 3-2 to 3-4 may not include a carbazole group.

In one or more embodiments, in Formula 3-3, R₈₁ and R₈₂ may be linked to each other via a single bond or a (dim ethyl)methylene group, and/or R₈₃ and R₈₄ may be linked to each other via a single bond or a (dimethyl)methylene group (for example, see Compound H2-27 below).

In one or more embodiments, in Formula 3-4, R₈₁ and R₈₂ may be linked to each other via a single bond or a (dim ethyl)methylene group, and/or R₈₃ and R₈₄ may be linked to each other via a single bond or a (dimethyl)methylene group, and/or R₈₅ and R₈₆ may be linked to each other via a single bond or a (dimethyl)methylene group.

In one or more embodiments, the Pt-containing organometallic compound may be a compound represented by Formula 1-1 or 1-2:

##STR00087##

In Formulae 1-1 and 1-2,

M, Y₁ to Y₄, X₁ to X₄, and T₁ to T₃ may each be the same as described above,

X₁₁ may be N or C-[(L₁₁)_b11-(R₁₁)_c11], X₁₂ may be N or C-[(L₁₂)_b12-(R₁₂)_c12], X₁₃ may be N or C-[(L₁₃)_b13-(R₁₃)_c13], and X₁₄ may be N or C-[(L₁₄)_b14-(R₁₄)_c14],

L₁₁ to L₁₄, b11 to b14, R₁₁ to R₁₄, and c11 to c14 may each be the same as defined in connection with L₁, b1, R₁, and c1, respectively,

X₂₁ may be N or C-[(L₂₁)_b21-(R₂₁)_c21], X₂₂ may be N or C-[(L₂₂)_b22-(R₂₂)_c22], and X₂₃ may be N or C-[(L₂₃)_b23-(R₂₃)_c23],

L₂₁ to L₂₃, b21 to b23, R₂₁ to R₂₃, and c21 to c23 may each be the same as defined in connection with L₂, b2, R₂, and c2, respectively,

X₂₉ may be O, S, C(R₂₇)(R₂₈), Si(R₂₇)(R₂₈), or N-[(L₂₉)_b29-(R₂₉)_c29],

R₂₇ to R₂₉ may each be the same as defined in connection with R₂, and L₂₉, b29, and c29 may each be the same as defined in connection with L₂, b2, and c2, respectively,

X₃₁ may be N or C-[(L₃₁)_b31-(R₃₁)_c31], X₃₂ may be N or C-[(L₃₂)_b32-(R₃₂)_c32], and X₃₃ may be N or C-[(L₃₃)_b33-(R₃₃)_c33],

L₃₁ to L₃₃, b31 to b33, R₃₁ to R₃₃, and c31 to c33 may each be the same as defined in connection with L₃, b3, R₃, and c3, respectively,

X₄₁ may be N or C-[(L₄₁)_b41-(R₄₁)_c41], X₄₂ may be N or C-[(L₄₂)_b42-(R₄₂)_c42], X₄₃ may be N or C-[(L₄₃)_b43-(R₄₃)_c43], and X₄₄ may be N or C-[(L₄₄)_b44-(R₄₄)_c44],

L₄₁ to L₄₄, b41 to b44, R₄₁ to R₄₄, and c41 to c44 may each be the same as defined in connection with L₄, b4, R₄, and c4, respectively,

two of R₁₁ to R₁₄ may optionally be linked to form a C₅-C₃₀ carbocyclic group unsubstituted or substituted with at least one R_10a or a C₁-C₃₀ heterocyclic group unsubstituted or substituted with at least one R_10a,

two of R₂₁ to R₂₃ may optionally be linked to form a C₅-C₃₀ carbocyclic group unsubstituted or substituted with at least one R_10a or a C₁-C₃₀ heterocyclic group unsubstituted or substituted with at least one R_10a,

two of R₃₁ to R₃₃ may optionally be linked to form a C₅-C₃₀ carbocyclic group unsubstituted or substituted with at least one R_10a or a C₁-C₃₀ heterocyclic group unsubstituted or substituted with at least one R_10a, and

two of R₄₁ to R₄₄ may optionally be linked to form a C₅-C₃₀ carbocyclic group unsubstituted or substituted with at least one R_10a or a C₁-C₃₀ heterocyclic group unsubstituted or substituted with at least one R_10a.

In the present specification, examples of “the C₅-C₃₀ carbocyclic group unsubstituted or substituted with at least one R_1a” and “the C₁-C₃₀ heterocyclic group unsubstituted or substituted with at least one at least one R_1a” include a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, an adamantane group, a norbornene group, a cyclopentene group, a cyclohexene group, a cycloheptane group, a cyclooctene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group, a bicyclo[2.2.2]octane group, a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphtho pyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, an acridine group, a dihydroacridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyrrolophenanthrene group, a furanophenanthrene group, a thienophenanthrene group, a benzonaphthofuran group, a benzonaphthothiophene group, an (indolo)phenanthrene group, a (benzofurano)phenanthrene group, and a (benzothieno)phenanthrene group, each unsubstituted or substituted with at least one at least one R_1a, but embodiments of the present disclosure are not limited thereto.

In the present specification, examples of “the C₁-C₆₀ alkyl group” include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group, but embodiments of the present disclosure are not limited thereto.

In the present specification, examples of “the C₃-C₁₀ cycloalkyl group” include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, and a bicyclo[2.2.2]octyl group, but embodiments of the present disclosure are not limited thereto.

The Pt-containing organometallic compound may be one of Compounds 1-1 to 1-88, 2-1 to 2-47, 3-1 to 3-591, and D1 to D24, but embodiments of the present disclosure are not limited thereto:

##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159##

##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## ##STR00213## ##STR00214##

##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251## ##STR00252## ##STR00253##

##STR00254## ##STR00255## ##STR00256## ##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261## ##STR00262## ##STR00263## ##STR00264## ##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271## ##STR00272## ##STR00273## ##STR00274## ##STR00275## ##STR00276## ##STR00277## ##STR00278##

The first compound may be one of Compounds H1-1 to H1-75, but embodiments of the present disclosure are not limited thereto:

##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290## ##STR00291##

The second compound and the third compound may each independently be one of Compounds H2-1 to H2-73, but embodiments of the present disclosure are not limited thereto:

##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315##

In one or more embodiments, the composition may satisfy Equation 1 and Equation 2:
HOMO(H2)>HOMO(D)  Equation 1
HOMO(H3)>HOMO(D).  Equation 2

In Equations 1 and 2,

HOMO (H2) is an absolute value of the HOMO energy level of the second compound,

HOMO (H3) is an absolute value of the HOMO energy level of the third compound, and

HOMO (D) is an absolute value of the HOMO energy level of the Pt-containing organometallic compound.

In one or more embodiments, the difference between the absolute value of the HOMO energy level of the second compound and the absolute value of the HOMO energy level of the Pt-containing organometallic compound may be 0.05 eV to 0.6 eV, for example, 0.05 eV to 0.3 eV, and the difference between the absolute value of the HOMO energy level of the third compound and the absolute value of the HOMO energy level of the Pt-containing organometallic compound may be 0.05 eV to 0.6 eV, for example, 0.05 eV to 0.3 eV.

A weight ratio of the second compound to the third compound may be 9:1 to 1:9, for example, 2:7 to 7:2, but embodiments of the present disclosure are not limited thereto.

The composition including the Pt-containing organometallic compound, the first compound, the second compound, and the third compound may be suitably used for an organic layer, for example, an emission layer, in the organic light-emitting device. Another aspect of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the composition.

The organic light-emitting device includes the composition including the Pt-containing organometallic compound, the first compound, the second compound, and the third compound so that the organic light-emitting device may have improved external quantum luminescence efficiency, improved driving voltage, and improved lifespan characteristics.

The composition may be used between a pair of electrodes of the organic light-emitting device. For example, the emission layer may include the composition. Here, the Pt-containing organometallic compound may serve as a dopant, and the first compound, the second compound, and the third compound may each serve as a host.

The organic light-emitting device including the composition may emit red light, green light, or blue light. For example, the organic light-emitting device including the composition may emit green light, but embodiments of the present disclosure are not limited thereto.

The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.

In one or more embodiments, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

The term “organic layer” as used herein refers to a single layer and/or a plurality of layers between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including a metal.

The FIGURE is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. Hereinafter, the structure of an organic light-emitting device according to an embodiment and a method of manufacturing an organic light-emitting device according to an embodiment will be described in connection with the FIGURE. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.

A substrate may be additionally disposed under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

The first electrode 11 may be formed by, for example, depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may comprise a material with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-reflective electrode, or a transmissive electrode. The material for forming the first electrode 11 may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).

The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 11 is not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11 and the emission layer.

The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

The hole transport region may include only a hole injection layer or only a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11. For example, the hole transport layer comprises at least two layer.

When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.

When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10⁻⁸ torr to about 10⁻³ torr, and a deposition rate of about 0.01 Å/sec to about 100 Å/sec. However, the deposition conditions are not limited thereto.

When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 rpm to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.

The hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, a compound represented by Formula 202 below, or any combination thereof:

##STR00316## ##STR00317## ##STR00318## ##STR00319##

In Formula 201, Ar₁₀₁ and Ar₁₀₂ may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof.

In Formula 201, xa and xb may each independently be an integer from 0 to 5, or may be 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.

R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄ in Formulae 201 and 202 may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and the like), or a C₁-C₁₀ alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and the like);

a C₁-C₁₀ alkyl group or a C₁-C₁₀ alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group, or a salt thereof, or any combination thereof; or

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, or any combination thereof,

but embodiments of the present disclosure are not limited thereto.

In Formula 201, R₁₀₉ may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof.

In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:

##STR00320##

In Formula 201A, R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ may each be the same as described above.

For example, the compound represented by Formula 201 and the compound represented by Formula 202 may each be one of Compounds HT1 to HT20 or any combination thereof, but embodiments of the present disclosure are not limited thereto:

##STR00321## ##STR00322## ##STR00323## ##STR00324## ##STR00325## ##STR00326## ##STR00327##

A thickness of the hole transport region may be from about 100 Å to about 10,000 Å, for example, about 100 Å to about 3,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 10000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.

The charge-generation material may be, for example, a p-dopant. The p-dopant may comprise a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ) or F6-TCNNQ; a metal oxide, such as a tungsten oxide or a molybdenum oxide; and a cyano group-containing compound, such as Compound HT-D1 below, but are not limited thereto:

##STR00328##

The hole transport region may include a buffer layer.

Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.

Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may comprise a material for the hole transport region described above, a material for a host to be explained later, or any combination thereof. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained later.

Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a compound that is used to form the emission layer.

The emission layer may include the composition including the Pt-containing organometallic compound, the first compound, the second compound, and the third compound.

For example, the emission layer may include a dopant and a host, wherein the dopant includes the Pt-containing organometallic compound, and the host includes the first compound, the second compound, and the third compound.

Meanwhile, the emission layer may further include, in addition to the composition, another dopant and/or another host.

When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.

When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 20 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

An electron transport region may be disposed on the emission layer.

The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, Bphen, BAlq, or any combination thereof, but embodiments of the present disclosure are not limited thereto:

##STR00329##

A thickness of the hole blocking layer may be from about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a substantial increase in driving voltage.

The electron transport layer may include BOP, Bphen, Alq₃, BAlq, TAZ, NTAZ, or any combination thereof:

##STR00330##

In one or more embodiments, the electron transport layer may include one of ET1 and ET25, or any combination thereof, but are not limited thereto:

##STR00331## ##STR00332## ##STR00333## ##STR00334## ##STR00335## ##STR00336## ##STR00337## ##STR00338##

A thickness of the electron transport layer may be from about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.

Also, the electron transport layer may further include, in addition to the materials described above, a metal-containing material.

The metal-containing material may include a Li complex. For example, the Li complex may comprise ET-D1(Liq), ET-D2, or any combination thereof:

##STR00339##

The electron transport region may include an electron injection layer that promotes flow of electrons from the second electrode 19 thereinto.

The electron injection layer may include LiF, a NaCl, CsF, Li₂O, BaO, or any combination thereof.

A thickness of the electron injection layer may be from about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When a thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without substantial increase in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may comprise a metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the second electrode 19. To manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

Hereinbefore, the organic light-emitting device according to an embodiment has been described in connection with the FIGURE.

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term “C₁-C₆₀ alkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₆₀ alkyl group.

The term “C₁-C₆₀ alkoxy group” used herein refers to a monovalent group represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C₂-C₆₀ alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀ alkenylene group” as used herein refers to a divalent group having the same structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C₂-C₆₀ alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C₂-C₆₀ alkynylene group” as used herein refers to a divalent group having the same structure as the C₂-C₆₀ alkynyl group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C₃-C₁₀ cycloalkylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₂-C₁₀ heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one N, O, P, Si, Se, Ge, B, or S as a ring-forming atom and 2 to 10 carbon atoms, and non-limiting examples thereof include a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C₂-C₁₀ heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C₂-C₁₀ heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀ cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₂-C₁₀ heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one N, O, P, Si, Se, Ge, B, or S as a ring-forming atom, 2 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C₂-C₁₀ heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C₂-C₁₀ heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₂-C₁₀ heterocycloalkenyl group.

The term “(C₁-C₁₀ alkyl)carbazolyl group,” as used herein refers to a carbazole group substituted with a C₁-C₁₀ alkyl group.

The term “di(C₁-C₁₀ alkyl)′X′ group” as used herein refers to a ‘X’ group substituted with two C₁-C₁₀ alkyl groups.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C₆-C₆₀ arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C₆-C₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene group each include two or more rings, the rings may be fused to each other.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalent group having a cyclic aromatic system that has at least one N, O, P, Si, Se, Ge, B, or S as a ring-forming atom, in addition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group” as used herein refers to a divalent group having a cyclic aromatic system that has at least one N, O, P, Si, Se, Ge, B, or S as a ring-forming atom, in addition to 1 to 60 carbon atoms. Non-limiting examples of the C₁-C₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group each include two or more rings, the rings may be fused to each other.

The term “C₆-C₆₀ aryloxy group” used herein indicates —OA₁₀₂ (wherein A₁₀₂ is the C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group used herein indicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed to each other, a heteroatom N, O, P, Si, Se, Ge, B, or S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₃₀ carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C₅-C₃₀ carbocyclic group may be a monocyclic group or a polycyclic group.

The term “C₁-C₃₀ heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, Se, Ge, B, or S other than 1 to 30 carbon atoms. The C₁-C₃₀ heterocyclic group may be a monocyclic group or a polycyclic group.

A substituent of the substituted C₅-C₃₀ carbocyclic group, the substituted C₂-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), or any combination thereof;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), or any combination thereof;

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), or —P(═O)(Q₃₈)(Q₃₉), or any combination thereof.

In the present specification, Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ may each independently be hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C₁-C₆₀ alkyl group unsubstituted or substituted with deuterium, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or any combination thereof; a C₂-C₆₀ alkenyl group; a C₂-C₆₀ alkynyl group; a C₁-C₆₀ alkoxy group; a C₃-C₁₀ cycloalkyl group; a C₂-C₁₀ heterocycloalkyl group; a C₃-C₁₀ cycloalkenyl group; a C₂-C₁₀ heterocycloalkenyl group; a C₆-C₆₀ aryl group unsubstituted or substituted with deuterium, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or any combination thereof; a C₆-C₆₀ aryloxy group; a C₆-C₆₀ arylthio group; a C₁-C₆₀ heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

Hereinafter, the compound and the organic light-emitting device according to embodiments are described in detail with reference to Synthesis Example and Examples, but are not limited thereto. The wording “‘B’ was used instead of ‘A’” as used in describing Synthesis Example means that an amount of ‘A’ used was identical to an amount of ‘B’ used, in terms of a molar equivalent.

EXAMPLES

Synthesis Example 1 (Synthesis of Compound 3-348)

##STR00340##

Synthesis of Ligand 3-348C

2.1 g (0.005 mmol, 1.2 equiv.) of Intermediate 3-348B, 2.2 g (0.004 mol, 1 equiv.) of Intermediate 3-348A (i.e., 2-(1-([1,1′-biphenyl]-2-yl)-4-bromo-1H-benzo[d]imidazol-2-yl)-4,6-di-tert-butylphenol), 1.2 g (0.001 mmol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium (0), and 1.7 g (0.012 mmol, 3 equiv.) of potassium carbonate were dissolved in 20 mL of a solvent in which tetrahydrofuran (THF) and distilled water (H₂O) were mixed at a volume ratio of 3:1, and the mixed solution was refluxed for 12 hours. A temperature of the product obtained therefrom was cooled down to room temperature, and a precipitate was filtered. A resulting filtrate was washed with ethylene acetate (EA)/H₂O, and then, subjected to column chromatography (while increasing a volume rate of EN hexane (Hex) to between 20% and 35%), thereby obtaining 2.0 g (yield: 72%) of Ligand 3-348C. The product was identified by Mass Spectrum and HPLC.

HRMS(MALDI) calcd for C₅₄H₅₃N₃O: m/z 759.4189, Found: 759.4182.

Synthesis of Compound 3-348

2.0 g (2.38 mmol) of Ligand 3-348C and 0.98 g (2.38 mmol, 1.0 equiv.) of K₂PtCl₄ were dissolved in 80 mL of a solvent in which 60 mL of acetic acid (AcOH) was mixed with 20 mL of H₂O, and the mixed solution was refluxed for 16 hours. A temperature of the product obtained therefrom was cooled down to room temperature, and a precipitate was filtered and dissolved again in methylene chloride (MC). A resulting filtrate was washed with H₂O, and then, subjected to column chromatography (MC 40%, EA 1%, Hex 59%), thereby obtaining 1.1 g (purity: 99% or more, actual yield: 71%) of Compound 3-348. The product was identified by Mass Spectrum and HPLC.

HRMS(MALDI) calcd for C₅₄H₅₁N₃OPt: m/z 952.3680, Found: 952.3678.

Synthesis Example 2 (Synthesis of Compound 3-583)

##STR00341##

Synthesis of Ligand 3-583C

2.2 g (0.005 mmol, 1.2 equiv.) of Intermediate 3-583B, 2.4 g (0.004 mol, 1 equiv.) of Intermediate 3-583A (i.e., 2-(4-bromo-1-(5-(tert-butyl)-[1,1′-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-4,6-di-tert-butylphenol), 1.2 g (0.001 mol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium (0), and 2.0 g (0.015 mol, 3.7 equiv.) of potassium carbonate were dissolved in 80 mL of a solvent in which THF and distilled water (H₂O) were mixed at a ratio of 3:1, and the mixed solution was refluxed for 12 hours. A temperature of the product obtained therefrom was cooled down to room temperature, and a precipitate was filtered. A resulting filtrate was washed with EA/H₂O, and then, subjected to column chromatography (gradient elution with EA/Hex 20%-35%), thereby obtaining 2.2 g (yield: 68%) of Ligand 3-583C. The product was identified by Mass Spectrum and HPLC.

HRMS(MALDI) calcd for C₅₉H₆₀D₃N₃O: m/z 832.5159, Found: 832.5161.

Synthesis of Compound 3-583

2.2 g (2.26 mmol) of Ligand 3-583C and 1.1 g (2.26 mmol, 1.0 equiv.) of K₂PtCl₄ were dissolved in 80 mL of a solvent in which 60 mL of AcOH was mixed with 20 mL of H₂O, and the mixed solution was refluxed for 16 hours. A temperature of the product obtained therefrom was cooled down to room temperature, and a precipitate was filtered and dissolved again in MC. A resulting filtrate was washed with H₂O, and then, subjected to column chromatography (MC 40%, EA 1%, Hex 59%), thereby obtaining 1.0 g (purity: 99% or more, actual yield: 68%) of Compound 3-583. The product was identified by Mass Spectrum and HPLC.

HRMS(MALDI) calcd for C₅₉H₅₈D₃N₃OPt: m/z 1025.4651, Found: 1025.4653.

Evaluation Example 1

HOMO energy levels of the compounds below were measured using a photoelectron spectrometer (for example, AC3 manufactured by RIKEN KEIKI Co., Ltd.) in air, and the results are shown in Table 1.

TABLE 1

         Actual measurement
Compound of HOMO energy level (eV)

3-348    −5.45
3-583    −5.43
H1-15    −5.95
H1-63    −6.07
H1-65    −6.12
H1-75    −6.07
HA1      −5.71
H2-2     −5.58
H2-71    −5.69
H2-72    −5.65
HA2      −5.35
HA3      −6.00

##STR00342## ##STR00343## ##STR00344## ##STR00345##

Example 1

A glass substrate on which an ITO electrode was prepared, was cut to a size of 50 mm×50 mm×0.5 mm, sonicated with acetone, isopropyl alcohol and pure water each for 15 minutes, and then, cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Next, F6-TCNNQ was deposited on the ITO electrode (i.e., an anode) of the glass substrate to form a hole injection layer having a thickness of 100 Å, HT3 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 1,260 Å, F6-TCNNQ and HT3 were co-deposited at a weight ratio of 5:95 on the first hole transport layer to form a second hole transport layer having a thickness of 100 Å, and HT3 was deposited on the second hole transport layer to form a third hole transport layer having a thickness of 300 Å.

Then, a host and a dopant were co-deposited at a weight ratio of 85:15 on the third hole transport layer to form an emission layer having a thickness of 400 Å. Here, as the host, a first compound (e.g., Compound H1-63), a second compound (e.g., Compound H₂-2), and a third compound (e.g., Compound H2-72) (wherein a weight ratio of the first compound, the second compound, and the third compound was 3:3.5:3.5), and as the dopant, Compound 3-348 was used.

Next, Compounds ET1 and ET-D1 were co-deposited at a weight ratio of 5:5 on the emission layer to form an electron transport layer having a thickness of 360 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 5 Å, Al was vacuum-deposited on the electron injection layer to form a second electrode (i.e., a cathode) having a thickness of 800 Å, thereby completing the manufacture of an organic light-emitting device having a structure of ITO/F6-TCNNQ (100 Å)/HT3 (1260 Å)/HT3: F6-TCNNQ (5 wt %) (100 Å)/HT3 (300 Å)/host: dopant (15 wt %) (400 Å)/ET1: ET-D1 (50 wt %) (360 Å)/LiF (5 Å)/Al (800 Å):

##STR00346##

Example 2 and Comparative Examples 1 to 4

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that compounds listed in Table 2 were each used as a host and a dopant in forming an emission layer.

Evaluation Example 2

The external quantum luminescence efficiency (EQE), driving voltage, and lifespan (T₉₅) of the organic light-emitting devices manufactured according to Examples 1 and 2 and Comparative Examples 1 to 4 were evaluated, and the results are shown in Table 2. Here, as a device used for the evaluation, a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used. The lifespan (T₉₅) (at 16,000 nit) was obtained by evaluating time (hr) that lapsed when luminance was 95% of initial luminance (100%). The EQE and the lifespan (T₉₅) were both measured at luminance of 16,000 cd/m².

	TABLE 2
	Host
					Difference (eV) between
					absolute value of HOMO
					energy level of second			Lifespan
					compound and absolute		Driving	(T95 at
		First	Second	Third	value of HOMO energy		voltage	16,000 nit)
	Dopant	compound	compound	compound	level of third compound	EQE (%)	(V)	(hr)
Example 1	3-348	H1-63	H2-2	H2-72	0.07	24.1	3.9	380
	Weight ratio = 3:3.5:3.5
Example 2	3-348	H1-63	H2-2	H2-71	0.11	23.4	4.0	375
	Weight ratio = 3:3:4
Comparative	3-348	H1-63	H2-2	—	—	23.8	3.9	250
Example 1		Weight ratio = 4:6
Comparative	3-348	H1-63	—	H2-72	—	23.1	4.4	365
Example 2		Weight ratio = 2.5:7.5
Comparative	3-348	H1-65	H2-2	—	—	23.6	4.0	280
Example 3		Weight ratio = 4:6
Comparative	3-348	HA1	HA2	HA3	0.65	19.5	4.3	20
Example 4		Weight ratio = 4:2:4

##STR00347## ##STR00348## ##STR00349##

Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 and 2 had high EQE, low driving voltage, and long lifespan characteristics, as compared with the organic light-emitting devices of Comparative Examples 1 to 4.

Examples 3 and 4

Organic light-emitting devices were manufactured in the same manner as in Examples 1 and 2, respectively, except that, Compound 3-583 was used instead of Compound 3-348 as a dopant in forming an emission layer.

Evaluation Example 3

The EQE, driving voltage, and lifespan (T₉₅) of the organic light-emitting devices of Examples 3 and 4 were evaluated in the same manner as in Evaluation Example 2, and the results are shown in Table 3.

	TABLE 3
	Host
					Difference (eV) between
					absolute value of HOMO
					energy level of second			Lifespan
					compound and absolute		Driving	(T95 at
		First	Second	Third	value of HOMO energy		voltage	16,000 nit)
	Dopant	compound	compound	compound	level of third compound	EQE (%)	(V)	(hr)
Example 3	3-583	H1-63	H2-2	H2-72	0.07	25.5	3.8	500
	Weight ratio = 3:3.5:3.5
Example 4	3-583	H1-63	H2-2	H2-71	0.11	24.4	3.9	510
	Weight ratio = 3:3:4

##STR00350##

Referring to Table 3, it was confirmed that the organic light-emitting devices of Examples 3 and 4 had excellent EQE, excellent driving voltage, and excellent lifespan characteristics.

According to the one or more embodiments, the composition has excellent electric characteristics and excellent stability, and thus, an electronic device, for example, an organic light-emitting device, including the composition may have improved external quantum luminescence efficiency, improved driving voltage, and improved lifespan characteristics.

It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.

While one or more embodiments have been described with reference to the FIGURES, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.

Claims

1. A composition comprising a platinum-containing organometallic compound, a first compound, a second compound, and a third compound,

wherein the composition does not comprise iridium,

the Pt-containing organometallic compound, the first compound, the second compound, and the third compound are different from each other,

the first compound comprises at least one electron transport moiety,

the second compound and the third compound do not include a metal,

each of an absolute value of a homo energy level of the second compound and an absolute value of a homo energy level of the third compound is 5.30 eV to 5.85 eV,

the difference between the absolute value of the homo energy level of the second compound and the absolute value of the homo energy level of the third compound is 0.01 eV to 0.30 eV, and

each of the homo energy level of the second compound and the homo energy level of the third compound is measured using a photoelectron spectrometer in air.

2. The composition of claim 1, wherein

the Pt-containing organometallic compound comprises Pt and a tetradentate organic ligand, wherein the Pt and the tetradentate organic ligand form 3 or 4 cyclometallated rings.

3. The composition of claim 2, wherein

the tetradentate organic ligand comprises a benzimidazole group and a pyridine group.

4. The composition of claim 1, wherein

an absolute value of the homo energy level of the Pt-containing organometallic compound is 5.25 eV to 5.55 eV, and

the homo energy level of the Pt-containing organometallic compound is measured using a photoelectron spectrometer in air.

5. The composition of claim 1, wherein

the electron transport moiety is a cyano group, a fluoro group, a π-electron-deficient nitrogen-containing cyclic group, a group represented by one of the following formulae, or any combination thereof:

6. The composition of claim 1, wherein

at least one of the second compound and the third compound does not include an electron transport moiety.

7. The composition of claim 1, wherein

at least one of the second compound and the third compound independently comprises:

i) a condensed ring in which one or more fifth rings and one or more sixth rings are condensed with each other,

ii) a group represented by

8. The composition of claim 1, wherein

the Pt-containing organometallic compound is an organometallic compound represented by Formula 1,

the first compound is a compound represented by Formula 2, or

the second compound and the third compound are each independently represented by one of Formulae 3-1 to 3-4:

9. The composition of claim 8, wherein

in Formula 1, Y₁ is O or S, Y₂ to Y₄ are each a chemical bond, X₁ and X₃ are each C, and X₂ and X₄ are each N.

10. The composition of claim 8, wherein

Het1 in Formula 2 is a group represented by one of Formulae 2-1 to 2-42:

11. The composition of claim 8, wherein

a group represented by

12. The composition of claim 8, wherein

in Formula 1,

a1 to a4 are each independently an integer from 1 to 20, and

at least one of R₁ to R₄ is each independently a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), or —B(Q₆)(Q₇).

13. The composition of claim 8, wherein

i) L₇₅, L₇₉, and L₈₁ to L₈₇ in Formulae 3-1 to 3-4 are each independently a π-electron-rich C₃-C₃₀ cyclic group unsubstituted or substituted with deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a di(C₁-C₁₀ alkyl)fluorenyl group, a di(C₆-C₆₀ aryl)fluorenyl group, a dibenzosilolyl group, a di(C₁-C₁₀ alkyl)dibenzosilolyl group, a di(C₆-C₆₀ aryl)dibenzosilolyl group, a carbazolyl group, a (C₁-C₁₀ alkyl)carbazolyl group, a (C₆-C₆₀ aryl)carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, —N(Q₃₁)(Q₃₂), or any combination thereof, or ii) L₇₉ in Formula 3-1 is a single bond, R₇₁, R₇₂, R₇₅, R₇₆, and R₈₁ to R₈₆ in Formulae 3-1 to 3-4 are each independently:

hydrogen or deuterium;

a C₁-C₂₀ alkyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a di(C₁-C₁₀ alkyl)fluorenyl group, a di(C₆-C₆₀ aryl)fluorenyl group, a dibenzosilolyl group, a di(C₁-C₁₀ alkyl)dibenzosilolyl group, a di(C₆-C₆₀ aryl)dibenzosilolyl group, a carbazolyl group, a (C₁-C₁₀ alkyl)carbazolyl group, a (C₆-C₆₀ aryl)carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, —N(Q₃₁)(Q₃₂), or any combination thereof;

a π-electron-rich C₃-C₃₀ cyclic group unsubstituted or substituted with deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a di(C₁-C₁₀ alkyl)fluorenyl group, a di(C₆-C₆₀ aryl)fluorenyl group, a dibenzosilolyl group, a di(C₁-C₁₀ alkyl)dibenzosilolyl group, a di(C₆-C₆₀ aryl)dibenzosilolyl group, a carbazolyl group, a (C₁-C₁₀ alkyl)carbazolyl group, a (C₆-C₆₀ aryl)carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, —N(Q₃₁)(Q₃₂), or any combination thereof; or

—N(Q₁)(Q₂).

14. The composition of claim 8, wherein

the Pt-containing organometallic compound is a compound represented by Formula 1-1 or 1-2:

15. The composition of claim 1, wherein

the composition satisfies Equation 1 and Equation 2 below:

homo(H2)>homo(D)  Equation 1

homo(H3)>homo(D),  Equation 2

wherein, in Equations 1 and 2,

homo (H2) is an absolute value of a homo energy level of the second compound,

homo (H3) is an absolute value of a homo energy level of the third compound,

homo (D) is an absolute value of a homo energy level of the Pt-containing organometallic compound, and

the homo energy level of the Pt-containing organometallic compound is measured using a photoelectron spectrometer in air.

16. The composition of claim 15, wherein

the difference between the absolute value of the homo energy level of the second compound and the absolute value of the homo energy level of the Pt-containing organometallic compound is 0.05 eV to 0.6 eV, and

the difference between the absolute value of the homo energy level of the third compound and the absolute value of the homo energy level of the Pt-containing organometallic compound is 0.05 eV to 0.6 eV.

17. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode and including an emission layer,

wherein the organic layer includes the composition of claim 1.

18. The organic light-emitting device of claim 17, wherein

the emission layer includes the composition.

19. The organic light-emitting device of claim 18, wherein

the emission layer includes a dopant and a host,

the dopant includes the platinum-containing organometallic compound of the composition, and

the host includes the first compound of the composition, the second compound of the composition, and the third compound of the composition.

20. The organic light-emitting device of claim 18, wherein

the emission layer emits green light.